


Dean Winchester and the Patron Saint of Blind Dates

by goldenraeofsun



Category: Supernatural
Genre: Alternate Universe - Human, Angst with a Happy Ending, Bartender Castiel (Supernatural), Benny Lafitte & Dean Winchester Friendship, Blind Date, Dean Winchester Has Self-Worth Issues, Fluffy ending y'all, M/M, Minor Dean Winchester/Other(s), Minor Ruby/Sam Winchester, Mutual Pining, because i am weak
Language: English
Status: Completed
Published: 2020-01-07
Updated: 2020-01-07
Packaged: 2021-02-25 01:27:02
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 18,000
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22147786
Author URL: https://archiveofourown.org/users/goldenraeofsun/pseuds/goldenraeofsun
Summary: Dean Winchester's friends are a bunch of traitors. So he had a bad breakup two years ago and hasn't gotten back on the horse. Their intervention - a series of blind dates - can't be the solution.But if this'll get his friends to stop, Dean can choke down over-priced spaghetti, make forced conversation, and drink whatever random cocktail the blue-eyed weirdo bartender makes for him next.At least Cas has his back. One nod from Dean, and he'll swoop down from behind the bar and make excuses for Dean to bail. It would be a perfect system - except Dean can't stop trading knowing looks with Cas and focus on his damn dates instead.
Relationships: Castiel/Dean Winchester
Comments: 100
Kudos: 791
Collections: The Destiel Fan Survey Favs Collection





	1. Chapter 1

**Author's Note:**

> An enormous thank you goes out to my betas, wordcluster9 and Annalea. You guys are awesome!

Ruby’s head whips around like the girl in the Exorcist. With a new bowl of popcorn cradled in one arm, she asks gleefully, “Dean’s going on a date with _who?”_

“Nobody,” Dean cuts in before Sam, Charlie, or Jo can butt in. “Dean’s going on a date with nobody,” he repeats with a glare around the room for good measure. He turns back around in his seat to stare straight ahead at the television showing a panoramic view of the Forest Moon of Endor. A pointed move to get them back on track. They can’t spend the _whole_ movie talking about Dean’s lackluster love life, especially with a young Harrison Ford prancing around on screen, dodging and weaving storm trooper blasters like the ultimate badass. 

Jo slaps him on the side of the head.

“Ow!”

Charlie makes a “pfft!” sound and high-fives Jo. “Dean doesn’t know who yet. It’s a blind date!”

“Blind _dates_ ,” Jo corrects with a grin as she dances out of the way of Dean’s elbow, aimed squarely at her ribs. “He's going on more than one.”

Sam shifts on the couch to make enough room for Ruby to sit back down on his lap. “We want to get our money’s worth.”

Dean mimes gagging into his own bowl of popcorn.

Ruby’s face lights up. “Awesome,” she says in a hushed voice. “Who’s picking the lucky ladies?”

“Or dudes,” Charlie corrects with a frown. “We’re not limiting Dean’s chances of success by overlooking half the pool.”

Dean groans loudly. “You can forget the whole damn pool. I’m not doing it.”

“You’re going.” Jo points a Twizzler threateningly at his jugular. “Or, so help me god, I’ll tell Mom you were the one who trashed the Roadhouse bathroom after your senior year.” She rips into the Twizzler with a vicious snap of teeth.

Dean swallows. “Bring it on, Blondie. I’m not afraid of Ellen.”

Jo guffaws as she trades a loaded look with Sam. He adds, “And I’ll tell Bobby who really put that dent in his old pickup and _how_ you did it.”

Dean gapes at them, betrayed. He throws up his hands, nearly knocking the rest of his popcorn to the floor. “What the hell did I ever do to all of you?”

Charlie rolls her eyes. “Relax, it’s a couple of blind dates. We’re not dumping you into the Pit of Despair.”

“Sure seems like it,” Dean grumbles. “At least then there’d be some Cary Elwes in it for me.”

“That’s why!” Sam says as he wraps a possessive arm around Ruby’s waist, keeping her in place. “You’re lonely. We’ve all noticed.”

“I’m not lonely,” Dean scoffs.

They _all_ make noises of disbelief, the traitors.

“I can’t believe you’re ganging up on me on movie night.” Dean gestures to the television screen. “If Benny was here, he’d back me up.”

Jo wipes away a fake tear. “Oh no, too bad we picked a movie night when Benny had to work.”

Dean’s mouth hangs open in horror. This shit was _planned?_ What kind of backstabbing sons of bitches...? 

Except Ruby. He’s not surprised in the least she’s all in for this horror show. Ruby has always had it out for Dean ever since he made it clear she doesn’t deserve Sam; do not pass go, do not collect two-hundred dollars. Admittedly, it was a bad move on Dean’s part to tell her the night before the engagement party, but if not then, when? The day before the wedding? _During_ the wedding? Dean’s an asshole. Not the worst person on the planet.

And _if_ Dean has been going through a bit of a dry spell, it’s no one’s business but his own. Amara had acted like a complete psycho when they’d split two years ago, but he’d gotten over it. She’d gotten over it - at least, she’s been obeying the restraining order. Dean is back in his normal routine. If he isn't picking up randos in bars yet, he’ll get his groove back eventually.

Dean’s eyes narrow at all of them. “Is this an intervention?”

A split second of silence.

“No,” Sam lies, his face earnest. 

“Yes,” Charlie says at the same time. 

Jo facepalms.

Ruby grins. “I think it’s a great idea. There's a couple of people I’d love to set you up with.”

“Are any of them serial killers?”

Ruby’s eyes gleam. “If they are, they haven’t gotten caught yet.” 

“And this,” Dean sweeps an arm in Sam-and-Ruby’s direction, “is why I learned what roofies look like. I’m not gonna end up with my hotel bathtub with my kidney carved out in Chechnya. No dates.”

“Just ‘cause Amara-”

Jo starts. “Ruby!”

Charlie glares. “Hey!”

Sam pokes her in the side. “What’d we say about the A-word?”

“What?” Ruby makes a face at all them. “You all were the ones who wanted to treat him with kid gloves. _I_ didn’t want to baby him. He’s not going to get over her if we talk about her like she’s Voldemort.”

“I am over her,” Dean says firmly.

Sam shoots him a pitying look. “If you are, what could it hurt going out with a few new people?”

“My wallet, for one.”

“We’ll split the bill with you,” Charlie says.

“We will?” Ruby asks, eyebrows raised in surprise.

“We will,” Jo repeats in a steely tone before adding to Dean, “if that’s an issue.”

Dean exhales a loud sigh, shoulders slumping. He can’t really be doing this. “How many dates are we talking about?” he asks.

Sam sits up a little straighter, and Ruby glares at him for disturbing her seat. “A couple dates each. No more than two.”

Between Sam, Jo, Charlie, and Ruby, that’s eight fucking dates - _at minimum,_ since Dean doesn’t trust Ruby or Jo to cheat some way or another.

“I get to choose the place,” Dean relents. “I’m serious. I don’t want any of you spying on me.”

Ruby offers Sam a piece of popcorn, asking in a faux-casual voice, “What, afraid of a little performance anxiety?”

Dean glares. “Can it.” 

Charlie claps her hands, and Dean breaks his staring contest with the demon sitting on his brother’s lap. “Great! I think my friend Aaron’s free next Friday.”

“Great,” Dean echoes hollowly.

**BELA TALBOT**

Aaron is not free next Friday. But Sam’s lawyer friend, Bela is.

Dean picks the fancy but moderately-priced (still out of his usual dollar range, though) Italian place across the street from the Roadhouse. Bela is an Italian name, right? That’s got to be a better choice than any of Dean’s usual haunts.

He gets there fifteen minutes early and heads straight for the bar. Social lubricant, liquid courage, whatever you want to call it - Dean needs it down the hatch. Pronto.

He flags down the bartender immediately. Thankfully he’s not busy.

“What can I get you?” he asks, his voice as low as Dean’s self-esteem and blood alcohol content.

Dean glances lovingly at a tray of fancy cocktails passing by, every color of the rainbow. “Booze. Lots of it.” At the bartender's confused frown, Dean rolls his eyes. "Just surprise me, dude."

The bartender’s forehead furrows. “Do you want anything in particular? I confess, if I choose for you there’s a strong likelihood you wouldn’t like it.”

Dean throws him a judging look. “Isn’t that what bartenders are supposed to do best?”

“It’s my first day,” the bartender says, his face deadpan.

“Really?”

“No.”

A laugh forces itself out of Dean’s mouth despite himself.

“It is my third, though,” the bartender continues, “and my first shift with more than the ‘regulars.’”

Dean hasn’t seen finger quotes in just about forever, and that alone is enough to keep the smile lingering on his lips. Dean shakes his head. “I swear, I couldn’t care less what you give me.”

“Alright then,” the bartender says in a heavy voice. “Please keep in mind, you asked for this.”

Dean watches him work, pouring things and shaking other things. He’s not very artistic about it - more competently businesslike, which Dean can get behind. If the guy’s new, then he definitely shouldn’t be trying any fancy waterfalls or, heaven forbid, fire. The bartender has damn nice hands, long-fingered and slender, like Dean prefers in all his partners. There’s no ring - 

And that’s the one thought Dean _shouldn’t_ be having right before a date with someone else.

Dean pulls out his phone and tries not to stare at the bartender like a creep. Dean steals glances instead - totally less weird if he doesn't get caught. 

Evidently this bartender is much less observant than the average human being, or he has a lot more than three days' experience being ogled and is totally cool with it. Whatever the reason, he doesn’t comment on Dean's secret perving except to say, “Here you go, sir.”

Dean stares. He doesn't take it. “Why is it purple?”

“It’s a Purple Nurple,” the bartender says, completely straight-faced, like those are perfectly normal English words to say in a sentence. 

“A what?”

“A Purple Nurple,” the bartender repeats, proving that Dean has indeed met the worst bartender in the great state of California. “Rum, triple sec, cranberry juice, and curacao.”

“Huh.”

“You were eyeing the drinks tray as it went by," the bartender explains. “And you seem like the sort of man who wouldn’t order this for himself.”

“That’s true.” Dean skeptically picks up the glass.

“Try it.”

“Lemme guess, if I don't like it, it’s on the house?”

“Of course not," the bartender says, affronted. “I can’t give away free drinks. That’s not how to run a successful business.”

Dean snorts and takes a tentative sip - and another when the first doesn't turn out terribly. It’s sweet and tart on his tongue, not a bad change from his usual beer or bottom shelf whiskey. "It’s okay.”

One corner of the bartender's mouth raises in a half smile. “I’m pleased to hear that.”

“I’ll have a whiskey next, though.”

The bartender frowns. 

“I might have to run soon.” Dean jerks his thumb over his shoulder. “It’s easier to down a whiskey than whatever this is.”

“A Purple Nurple,” the bartender reminds promptly. 

Dean cringes. “Dude, I’m not saying that in public.”

The bartender takes a couple steps towards the other end of the bar, where more patrons wait. “If you would like another, you know where to find me.”

Dean salutes him with the rest of his Purple Nurple. He licks his lips after his next pull - that taste really is something.

* * *

Dean can tell from the moment they order drinks (red wine, of course) that Bela is completely out of his league and she knows it. She eyes him appreciatively, though, while the waiter pours out the taster and Dean pretends to know anything at all about wine, mumbling his way through the uncomfortable, “Yeah, it’s good. Go ahead,” and handing the glass back.

“To first impressions?” Bela toasts as she raises her glass.

“To first impressions,” Dean agrees. He inches his glass forward, but she doesn’t move to clink, so he just retreats with his wine and tries to go for a medium sized-swallow. 

It’s much drier and much less enjoyable than the Purple Nurple.

“So, Dean Winchester,” Bela starts, and goddamn, why didn’t Sam warn him she was English. “Tell me all about yourself. Your brother speaks very highly of you.”

“It’s all lies,” Dean says automatically before he can stop himself. Bela doesn’t even crack a smile, and Dean’s mood sinks as his nerves skyrocket. “I, uh, am from Kansas. Grew up kind of all over. Moved out here when Sam got into Stanford.”

Bela swirls her wine around in the glass. “And did you go to university out here too?”

“Uh, no,” Dean says, and Bela just blinks at him. “Got my GED and went to trade school. I’m a mechanic. Everyone needs a mechanic out here.”

“That is true,” Bela acknowledges, the corners of her mouth dipping down ever so slightly. She probably takes company cars everywhere - she seems like the type. 

Not a great sign. Dean takes a large gulp of wine. “And you? Where are you from?”

“Oh I grew up all over, just like you.” 

Dean doesn’t have to be a genius to know she means the exact opposite. 

She continues, “Born in London but spent time in Paris and Zurich before I did my undergraduate degree at Cambridge - I wanted to specialize in antiquities, if you can believe it. Realized there was no future in that,” she sweeps her perfect hair back from her face, “and then attended Stanford Law. I specialize in property and estate sales now.”

Stunned almost speechless, Dean takes another fortifying sip of wine. “That’s very impressive.”

Bela coolly regards him across the table, and the silence itches like ants under his collar. He glances down at his menu instead. Where the hell is that waiter?

He cranes around in his seat, looking for the guy, Alfie, who poured their wine. Just out of eyesight but not earshot, Bela sighs gustily.

Alfie appears before too long, probably drawn to their table by the sheer force of Dean’s desperation. He rattles off a series of specials and doesn’t provide their prices so Dean stops listening.

Dean lets Bela order first, nodding along like a brainless moron as she asks for a fancy salad and pasta with vegetables Dean immediately dismissed out of principle.

When it’s Dean's turn, he starts, “I’ll go for the garlic bread-”

“Really?” she asks, eyebrows raised. “Garlic bread on a first date?”

“What?” he barks, more than a little defensive. “Garlic bread is delicious.” 

Judging by the way the evening is going, Dean’s not going to get a kiss out of Bela without crossing some serious moral lines or needing mouth-to-mouth resuscitation. Dean might be a dumbass, but he can read signs from a lady just fine.

Bela adopts a haughtily resigned expression and waves Dean forward to continue his order.

The date doesn’t improve as the night goes on.

Bela makes not-so-subtle jabs at Dean’s profession, his education, even his accent (even though Miss Pip-Pip-off-to-Tea-with-the-Queen shouldn’t really point fingers). 

Even worse, Dean can’t just lay it into her because they're in public. All he can do is sit there and stew in his own bad decisions. Sam better guard his shampoo bottle with his life next time Dean sleeps on his couch.

Dean eats his spaghetti bolognese hatefully. 

Not one minute after Bela polishes off her main course, her phone rings. 

“Sorry, this is an emergency,” she lies, deadpan and entirely transparent. 

“Of course.” Dean rolls his eyes as he gestures in her direction with a wide sweep of his hand. “By all means. If you have to go.”

Bela stands. “Well, it’s been a pleasure.”

Dean snorts derisively. “Just don’t promise to call first.”

For the first time that night, Bela looks relieved. “At least we’re on the same page about that. I’ll perhaps see you around, then.”

“Only if I lose another bet.”

Bela musters up the most unamused smile Dean has ever seen and wiggles her fingers in an approximation of a wave. 

Dean slumps in his seat and motions for the waiter to bring him the bill.

* * *

Dean calls his brother as soon as he gets back to his one-bedroom apartment. It’s almost nine o’clock at night now - Jeopardy! is long over, and Dean will never forgive Bela Talbot. The Tournament of Champions only comes around once a year. 

Sam barely answers the call before Dean barks, “What the hell dude?”

“Please tell me you’re not calling me while in bed with her,” Sam says wearily, apparently entirely on-board with skipping their usual phone call greeting: “hey bitch,” “hello to you too, Dean.”

“Like I’d touch her with a ten-foot pole! She’d probably chop my dick off anyway. Stop me from procreating and bringing down the rest of the human population.”

“That bad?”

“She’s a fucking monster, man.”

“She can’t be _that_ bad,” Sam wheedles, but Dean can hear the doubt in his voice alongside the noise of the television in the background.

Dean kicks off his shoes and flops down on his couch. “She basically called me a neanderthal because I didn’t go to a fancy Ivy League school.”

“Oh.”

“And now I’m like eighty bucks in the hole. Why the fuck did you think this was a good idea?”

Sam hesitates. “She’s hot?”

Dean actually pulls his phone away from his ear to gape at it. “Really? That’s what you think my standards are?”

“I don’t know, Dean! When was the last time you had a long-term relationship before your last one? Cassie in high school? Maybe Carmen, who I never met? That weird hate-relationship you had with the British guy when I was in law school?”

“Ketch?”

“Sure, whatever.” Canned laughter of a sitcom comes through in the background, fading as Sam walks away from the television. “But Dean, do you know what they had in common?”

“No?” Dean tries.

“Nothing! They had absolutely _nothing_ in common, so sue me, I had nothing to go on.” Sam quiets. “And we don’t really talk about this sort of stuff anymore.”

“Big swing and a miss, Sammy.”

“Like you wouldn’t have hate sex with her, given half a chance.”

“...You can’t prove anything.”

Sam sighs into the receiver. “At least give the next one a shot?”

“Hell no! No more blind dates.”

“What? You’ve been on only one so far. Charlie will kill us all if she doesn’t have her fair shot, at least.”

Dean runs a weary hand down his face. “Let me deal with Charlie.”

Sam chuckles. “It’s your funeral, man.”

**AARON BASS**

To the surprise of absolutely no one, Dean loses his argument with Charlie. Next Friday, he finds himself once again at a table at Angelo’s. Fuck it all, the lasagna looked good. And Charlie’s fucking loaded. She can afford to pay for it.

“Sorry I couldn’t make last week, man.” Aaron reaches over to shake Dean’s hand. “It was the Sabbath, you know.”

Dean frowns as they both sit. “But we were supposed to go out on Friday, not Sunday.”

Aaron fidgets with the sliver ware, clearly uncomfortable. “I’m Jewish… so, for me, the Sabbath starts Friday at sundown.”

“Ah,” Dean says, feeling distinctly wrong-footed.

“Yeah… so,” Aaron says slowly as if trying to figure out what to say next. “Unless you wanted our first date at my Opa’s with, like, fifty of my closest relatives, I thought I’d put it off for another week.”

Dean’s eyes almost bug out of his head. “You have a fifty-person dinner every week?”

Aaron laughs. “Fuck no, we’d drive Opa insane. It was Rosh Hashanah, so,” Aaron lifts his glass of wine, “Happy New Year!”

Dean musters a confused smile. “Happy New Year?”

“The Jewish one,” Aaron clarifies, like Dean couldn’t have sussed that one out for himself.

“Um, right.”

The date doesn’t get any less stilted from there. Aaron follows up with a question about Dean’s own religious background, and somehow Dean drops the bombshell that his mother was the most religious in their family and also the most dead - his brain doesn’t catch up with his mouth in time to stop that conversation-sinker. 

Aaron, unsurprisingly, doesn’t bring up another date as they grab the bill.

Dean, too sober for any of this, figures one drink for the road will do him a world of good and ambles up to the bar.

“What can I get you?” asks the same handsome bartender from last time.

Dean doesn’t care. “Surprise me.”

“You have no preference at all?”

“Whatever’s cheapest?” Dean tries as he slumps over the bar, shoulders hunched and head bowed.

In record time, a glass filled with bright amber liquid is being gently pushed under Dean’s nose. He takes a large gulp, shivering a little at the bitter burn and unexpected bubbles. Dean raises his head to murmur his thanks.

“You’re welcome. That’s a whiskey ginger, by the way. Whiskey and ginger ale.” The bartender hovers in front of him, his eyes darting nervously around the bar. 

There are a couple patrons in addition to Dean, but they all have half-empty or nearly full glasses in front of him. They are also all grouped in little groups of two or three... Dean shakes his head at his own morose thoughts about couples and takes another sip of his whiskey.

“Is everything alright?”

Dean frowns up at him. “I thought you were new at this.”

The bartender shrugs. “I’ve been on the job one week and a half.”

“It’s a bit early to play therapist, isn't it?”

“Really?” he asks, tilting his head as if he is actually considering Dean’s stupid question. “I thought it was what bartenders did.”

“Sure, but usually it takes ’em a bit longer to catch on that a friendly ear will score bigger tips.”

The bartender squints at Dean. “I thought it was what we were supposed to do. In all the movies-”

Dean cuts him off with a laugh. “That’s where you learned to tend a bar? Movies?”

“They didn’t cover interpersonal interaction at bartending school,” he says stiffly. 

Dean throws him an incredulous look, a smile spreading across his face and mood lightening. Because really, how is this guy even real? “So you figured movies were the best way to learn?”

“Yes,” he says, deadpan despite the faint blush spreading across his cheeks. 

Dean traces an idle finger over the rim of his glass. “Try television next time. Cheers.”

“Cheers to what?”

Dean laughs at his look of complete befuddlement. “No, dude, Cheers - the television show? Takes place in a bar?”

“Oh.”

“Did you grow up under a rock?”

“In a cult actually.”

Dean nearly spits out his drink. “Seriously?”

The bartender purses his lips. “Seriously.”

“Huh,” and Dean can’t tell if the bartender is fucking with him or not. Dean braces one elbow on the bar to study him. Not a single facial muscle tics. “Explains a lot.”

The bartender shrugs. “Fundamentalist Christian.”

It’s like Dean has been doused with a bucket of cold water. He shakes his head and waves off whatever the bartender is going to say next. “Fuck, please no more religion talk.” 

“No more?”

“It was my bad. He wanted to talk religion, and I’m not religious, but my mom was. Long story short, nothing tanks a first date like a dead mom. And now I’m unloading all this shit onto you. What a fucking cliche.” Dean tips back his drink.

The bartender glances around the bar again, and when nobody indicates they need him, turns back to Dean, leaning in a little closer. He says in a low voice, “Once, I told a date it wasn’t her fault her father ran off. He hated his job at the post office.”

Dean chuckles despite himself. “I bet that went over well.”

“It did not,” the bartender says placidly. “She threw her drink in my face and stormed off.”

“Were you together for a long time?”

“It was our first date.”

Dean snorts the rest of his whiskey ginger all over the bar. Nose burning, mouth swearing up a storm, Dean does his best to mop up the mess with wholly inadequate cocktail napkins until the bartender grabs a rag from beneath the bar and does a much better job of cleaning.

“You’re serious,” Dean gasps once his sinuses no longer feel like they’re on fire.

“You can ask the hostess.” The bartender tips his head towards the calm brunette who sat Dean and Aaron earlier. “Hannah saw the whole thing.”

Dean pushes his now empty glass away from him. “You have your dates here?”

The bartender shrugs. “I get a discount on the food. Would you like another whiskey?”

Dean shakes his head. “I should probably be heading home. Uh, thanks.”

“For what?”

Dean digs in his wallet for cash. Without looking up, he says, “I dunno. Making me laugh after a shitty night.”

“Well then,” the bartender says as he wipes down the bar one more time. “You’re welcome.”

Dean turns to go but stops. “What’s your name?”

“Cas.”

He holds out his hand. “Nice to meet you, Cas. I’m Dean.”

Cas grasps Dean’s proffered hand firmly. “It’s nice to meet you as well, Dean. Have a safe trip home.”

* * *

“It didn’t work out.”

Charlie looks up from her eggs and toast. “Aw, no way! I thought you’d hit it off.”

Jo, stopping by to top off their coffee, grins. “Eat it, Red. Your date sucked.”

Charlie asks, “What went wrong?”

Dean waits for Jo to move on to her next table, but she stays firmly rooted to the spot, her face expectant.

“We just didn’t click,” Dean mumbles. He shovels more waffle in his mouth. “It happens.”

The corners of Charlie’s mouth tug down into a pout. “But I was so sure he was it.”

Dean pours more maple syrup onto his already drenched plate. “Well, he wasn’t.”

Jo plops down onto the seat next to Charlie, across from Dean. He scowls at her and swallows down his food with difficulty, demanding with a mouth half-full, “Don’t you have people to wait on?”

Jo cranes her head around the Roadhouse, making a face at the scattered patrons. “They can sit tight for five minutes.”

“That’s no way to get tips, Joanna Beth.”

“Shut up. What was wrong with him?”

When in doubt, play dumb. A tried and true method for one Dean Winchester. “Who?”

Jo sets both elbows down on the table and stares at him like she's trying to read his mind. “The guy Charlie set you up with.”

“Nothing.”

“You can tell us,” Charlie says, leaning in. “He’s not a bestie or anything. He’s just one of my many subjects in Moondoor. Please tell me you were at least man enough to fess up to LARPing. I thought that was a surefire way for you two to bond.”

“It didn’t come up.”

Jo falls back in her seat. “Wow, you’re really bad at this.” She yelps as Charlie elbows her in the ribs. “I mean, what _did_ you talk about if not dress-up?”

“LARP is not _dress-up,”_ Charlie says icily to Jo before Dean can respond. “It’s a healthy outlet of escapism requiring keen senses of strategy and improvisation.”

Jo rolls her eyes. “Sure.”

Charlie huffs and points her fork in Dean’s direction. “We’re getting off track. What was wrong with Aaron?”

“Nothing!” Dean repeats. “He seemed like a nice guy. Everything was just awkward. I can’t explain it.”

Charlie’s mouth twists. “And you didn’t fuck it up somehow?”

“Why does it have to be my fault?” Dean demands.

“Because it’s _you,_ dork,” Jo says as she takes Charlie’s coffee spoon and swipes it through leftover maple syrup on Dean’s plate. She licks it clean as Dean looks away, disgusted, and Charlie goes a little pink. “If you don’t think something’s a good idea, you’ll personally fuck it up to prove yourself right.”

“Not the case here.”

Jo’s eyes narrow. “Oh yeah? Then what’d you guys talk about?”

“Religion.”

Jo and Charlie share a look.

“What else?” Jo asks eventually.

Dean cuts off another piece of waffle. “I told him my mom was into it ‘cause he brought up that he was Jewish. Like _really_ Jewish.” He shoves it into his mouth.

Jo makes a face. “Please don’t tell me you shared your dad’s insane conspiracy theory about your mom.”

“No, but conversation stalled pretty quick after I got into how she died.”

Charlie reaches over the table and whacks him on his arm. “That’s not first date talk!”

Dean recoils. “I know, alright? I panicked!”

“Why?” Charlie demands. “He’s not an intimidating dude. He’s like the _least_ intimidating dude I could find. And I’m counting Garth.”

Dean just sighs. “I’m out of practice, okay? It’s been a long while since I’ve been on a date with a guy.”

Jo turns to Charlie. “Who’s up next?”

“Ruby.”

Dean groans aloud.

“Come on,” Jo says. “They won’t be that bad… probably.”

“She hates me.”

Charlie’s expression turns sympathetic. “I’m sure she won’t knowingly send you out on a date with an axe murderer.”

“Maybe unknowingly, though,” Jo muses. “You know what kind of crowd she hangs out with.”

Dean viciously stabs another piece of waffle. “If you find my body hacked to pieces, you’ll know who to blame.”

**ALASTAIR**

For once, Dean isn’t the first to arrive at Angelo’s. Hannah shows him to his table where a tall, slender man waits. His cool blue eyes rake Dean up and down.

"Hello."

The hairs on the back of Dean's neck stand on end at hearing Alastair’s low purr. Still, he gamely sticks out his hand. 

Dean only has a split second of warning as Alastair firmly takes it. But instead of shaking his hand like a normal person, Alastair tugs Dean closer to kiss him on the cheek. Dean shivers as Alastair inhales deeply, his nose just next to Dean's right ear. 

What the fuck.

"Right," Dean says quickly as he tries to recover. "Hi."

Alastair positively leers at Dean over the table. "It's a pleasure to meet you and you. Ruby's description didn't do you justice."

"Oh, well," Dean says as he fiddles with his napkin and very deliberately does not look up, "she didn't say anything about you."

"There’s not much to talk about, I’m afraid," Alastair dismisses. He leans forward in his seat, eyes gleaming in the candlelight. "I'm much more interested in you, Dean Winchester."

Probably interested in wearing Dean's skin as a suit. 

Dean shakes off the thought and tries to meet Alastair's unwavering stare. "Not much here either," he says lightly. "I'm from Kansas. Moved out here when my brother started college. Trained mechanic." He stops as their waiter, Alfie - he served Dean before on his date with Bela - comes by.

"Ah," Alastair says, eyes only raising briefly to glance at their waiter before returning to Dean, "A man who works with his hands. I like that." He tips his head in Alfie's direction, finally allowing the kid to rattle off the specials and take their drink order. 

Dean orders a Purple Nurple just to fuck with Alastair. But Alastair barely seem fazed. He asks Alfie for their driest red.

“Now,” Alastair says as Alfie leaves. “Where were we?”

Dean blinks and grabs a breadstick for something to do with his hands. “I think we were talking about you, actually. How do you know Ruby?”

“She’s a client of mine.”

Dean nods along, amping up his minuscule interest to keep the conversation going. “What do you do?”

“I’m afraid that’s classified for now,” Alastair says with a chuckle. “Have to save some mystery for next time.”

Dean shoves more breadstick in his mouth. Another date with this skeezeball? He’d sooner give up apple pie for life. 

Alfie comes by with their drinks and Dean downs half of it in one go. Alastair watches him, eyes hooded. He traces on finger on the rim of his wine glass. “Would you like another?”

Dean swallows. “I’m good for now.”

“Yes, you are,” Alastair purrs as he reaches out to caress the back of Dean’s hand.

Dean jumps, knocking one of his knees into the table's underside. The whole thing rattles, nearly upending Alastair’s wine glass. “Sorry,” he mumbles as he retracts his hand to the safety of his own lap.

“It’s no trouble,” Alastair says calmly as he straightens his glass and fixes his silverware in perfectly parallel lines. “You seem nervous.”

Dean focuses anywhere but on Alastair’s face. He glares at the leaf garnish in his drink. “I’m fine.”

Alastair shrugs and raises his glass to take a careful sip. “It’s completely understandable if you are. We are just getting to know each other, after all.”

“Right.”

“But I do like to get some things out of the way right upfront,” Alastair continues. “I need to ensure compatibility with my partners, you know.”

“What, like blood type?” Dean asks out loud, like a complete dumbass.

For once, Alastair looks taken aback. “Not quite,” he says delicately. “More… inclinations, preferences. That sort of thing.”

“I like horror movies?” Dean tries.

Alastair leans in, his voice husky deep as he practically purrs, “More intimate than that.”

Dean’s eyebrows fly up to his hairline, pink satin popping into his mind’s eye despite his complete revulsion at the idea of combining Alastair and panties. He fumbles with his next sip of his drink, nearly dribbling half of it down his chin. He saves himself, just in time.

“Tell me, Dean-”

Dean represses a shiver at the way Alastair says his name.

“-Do you know that exquisite precipice between pain and pleasure?”

Dean stares at him, open-mouthed. He unsteadily sets his glass down before he drops the whole thing in his lap.

Alastair’s expression slowly turns predatory as Dean sits there, unspeaking.

Amara had liked pain too. She used to say her favorite pastime was to devour Dean, to take him apart so completely until there wasn’t a single part of him that wasn't hers. 

Dean had thought that was the hottest thing a chick had ever told him.

Dean before Amara was an idiot.

But Dean is now older and maybe a smidge wiser. He coughs, he mentally unscrambling his brain from that terrible trip down memory lane. “No. Not really.”

“It’s almost euphotic, or so I’ve been told by my partners,” Alastair adds as he reaches over to wrap his spindly fingers around Dean’s wrist.

Dean recoils, vaulting almost half out of his seat without conscious thought. 

Before he gets to his full height, freezing cold liquid spills over his head. Ice cubes fall with a clatter against the wooden floor. Chairs creak as neighboring tables turn around to see what happened. Heads swivel around.

Shocked, Dean shakes his head like a dog and hurriedly wipes the liquid out of his eyes. Shit, it’s starting to sting. He blinks rapidly, squinting at Cas standing in front of him, a half-full glass of Purple Nurple in hand.

“I’m so sorry, sir,” Cas says, his eyes wide. “I was just bringing you refills.” He bends down to pick up the glass, thankfully unbroken, and plunks the ice cubes back in.

They didn’t order refills. Dean hadn’t even finished his first one.

“It’s fine,” Dean says as he glances at Alastair out of the corner of his eye. “I, uh, should have watched where I was going.”

“It’s going to stain,” Cas points out as he straightens up.

Fucking Purple Nurples.

“I think I have some stain remover in the back, if you would like to follow me,” Cas says.

“Yes, of course.” Dean nearly trips over his feet to dog Cas’s steps. “Be right back, dude!” he calls over his shoulder at Alastair. He doesn’t look back to catch his reaction.

* * *

“I’m sorry,” Cas repeats as he closes the door behind Dean. 

“Don’t be,” Dean says brusquely as he plucks his shirt splattered with Purple Nurple away from his chest to inspect the damage. Cas hands him a few cloth napkins to dry off. “You saved me the hassle of getting away from that guy on my own.”

“I was aiming for your lap, if that’s any consolation,” Cas says, and Dean looks up from rubbing the napkin through his hair to see Cas wringing his hands. Cas gestures at Dean’s pants. “They’re dark enough not to leave visible stains.”

“You deliberately spilled this shit on me?”

Lips pressed into a tight line, Cas avoids Dean’s gaze. “You looked very uncomfortable with that man.”

Dean snorts a disbelieving laugh, a grin spreading across his face. “You’re a fucking godsend, you know that? Best bartender I’ve ever met.”

Cas blinks at him, stunned. 

“I was gonna fake food poisoning or something,” Dean continues, “but that would’ve meant sticking around until the main course. Your plan was way better.”

“Oh, well then,” Cas says, adorably flustered. “I’m glad I could help.”

Dean smirks. “Do you have that stain remover, though? I do actually need it.”

Cas whips a detergent stick out from an apron pocket. The fucker had it on him the whole time.

As Dean works out the dark splotches, he says, “Don’t have a lot of nice shirts to begin with, and if I have to do dry cleaning before my next date, I’m gonna be pissed. And no way is Ruby paying for any of that shit.”

“Ruby?”

“She’s the reason I’m out with that sadist.” Dean jerks his head towards the door and the restaurant beyond.

Cas shifts his weight to his other foot, at once contemplative and cautious. “If you don’t mind me asking, why did you agree to have dinner with him in the first place?”

“Blind date,” Dean explains with a grimace. “Believe me, if I had known a single thing about that dude - just one - I would’ve nixed it at the get-go. Guy’s a creep.”

“Have they all been blind dates? Every time you’ve come here it’s been with a different person.”

Dean smirks. “You’ve been watching me?”

“Unhappy people don’t tip,” Cas says primly.

Dean snorts and hands over the stain remover stick. “I always tip, dude. I’ve been a bartender and a waiter. I know how it goes.”

“Oh,” Cas says, startled. “Where do you work?”

“I’m not doing that anymore,” Dean says, waving off his concerns. “But I used to for a couple of years while my little brother was in college. Textbooks ain’t cheap.”

“No, they are not,” Cas agrees heavily, shoulders slumping.

“You too?” Cas looks older than Dean by several years. 

“Graduate student,” Cas says wryly. “I also got a late start on my undergraduate degree.”

“Oh.”

“With the whole cult, thing,” Cas adds, and holy shit, how did Dean forget that tidbit of background info on his favorite bartender.

Dean glances at the door. Alastair is probably still waiting, but fuck it. Talking to Cas beats Shades of Grey out there any day. “What are you studying?”

“Religious studies,” Cas says, mouth pursed.

Dean makes a face. Religion, again. “Enjoy it?” he asks half-heartedly as he tries to muster up enthusiasm.

“Usually,” Cas says, looking marginally happier. “I wish it paid better.” He gestures to his uniform, frowning a bit as he fingers an oily stain on his tie. He works the knot, and Dean can’t look away from the revealed sliver of Cas’s throat in the dimly lit back room. As Cas pulls the tie completely free, a glint of metal catches Dean’s eye. A slim silver chain, adorned by a simple cross.

Dean looks away, his heart sinking. Right. Fundamentalist Christian upbringing. Religious studies graduate student. Cas might as well be sporting wings and a halo for how out-of-bounds he is.

Dean glances down at his own navy tie. It doesn't exactly match, but it’s close. “I’ll trade you,” he says. “I don’t plan on sticking around, and I assume your shift’s not over yet.”

Cas shakes his head. “I was just going to go without and hope Hannah wouldn’t notice.”

Dean loosens his tie and slips it over his head, knot still intact, and hands it over to Cas. “Here,” Dean says, satisfied as Cas takes it from him. “I owe you, anyway.”

Cas narrows his eyes. “That’s not why I helped.”

“Yeah, but it makes my conscience feel better, so go with it.” Dean’s joking expression falters, darkening. “It’s not like I won’t be here to get it back next weekend, anyway.”

“Another date?”

“Yeah.”

Cas tilts his head, studying Dean thoughtfully. “Why do you go on them? You’ve never seemed particularly happy.”

“Part of a deal with my friends.” Dean grimaces. “They said I need to get out there. Start dating again.” Dean shrugs, looking away. “I had a bad break up,” he mutters, crossing his arms across his chest.

Cas’s mouth twists. “I’m not sure I see what you’re getting out of this other than overpriced food and terrible company.”

“Dude, that’s what I keep telling them.”

Cas opens his mouth, closes it again. Eventually, he says, without meeting Dean’s gaze, “If you insist on having them here, I might as well keep an eye out for you. I promise I won’t spill anything on you again.”

Dean freezes, unexpectedly touched. “You’d do that? Have my back for all the psychos my friends think are perfect for me?”

Cas shrugs. “You tip very well.”

Dean shores up a cocky grin. “Ah, that’s what’s in it for you.”

Cas’s deadpan expression doesn’t twitch. “You caught me.”

“Then you’ve got yourself a deal.”

**LISA BRAEDEN**

Dean doesn’t speak to Sam for a whole week after the Alastair shitshow. It’s the best he can do, since he only interacts with Ruby when forced and can’t punish her first-hand except through Sam. If Sam’s miserable, then Ruby’s at least got to be feeling a little of it.

Jo’s choice of blind date is amenable to meeting at Dean’s now regular Italian place. He feels marginally better about this one - not just because he gets to see Cas again. After their little talk in the backroom, this whole ordeal doesn’t seem as bad.

Hell, Jo showed Dean a picture of Lisa, and she ticks off all his superficial boxes - dark hair, bright eyes, a nice smile.

He gets to Angelo’s twenty minutes early and makes a bee-line for the bar. 

Cas is on him in an instant. “What can I get you?”

“Surprise me.”

He throws Dean a disgruntled look. “It will be much easier if you choose for yourself.”

“It worked out fine last time.”

“It ended up all over your shirt,” Cas says flatly.

“It worked out the first time, then,” Dean amends.

Cas rolls his eyes and stalks off, giving Dean ample time to admire Cas’s forearms (bare since he has his sleeves rolled up) and hands at work. He returns less than a minute later, depositing a red-orange drink in front of Dean.

“It’s a sazerac,” Cas says as Dean raises the drink to inspect it. Tentatively, he sniffs it. Smells like whiskey. “Whiskey based,” Cas continues, and that explains it, “but with added sugar, bitters, and absinthe. For you, I added a bit more sugar. You can’t tell just from looking at it, though.”

“Good man,” Dean says with a grin, tipping the glass in Cas’s direction before taking a sip. “Not bad. I like this better than the last one.”

Cas just shakes his head. “At least I’m getting closer,” he says sourly.

“Buck up, buddy,” Dean says after taking another, bigger, sip. “By my count, you’ve got another four tries at least to find me the perfect drink.”

Cas’s eyebrows raise. “Is that how many dates you have left?”

“One point for college boy.”

Cas glances around the bar. “I have to serve other guests. Will you be alright?”

“I don’t need a babysitter to drink my alcohol.” Dean throws up a little two-fingered salute to send Cas off. “Don’t worry.”

Cas tosses him a suspicious look over his shoulder but still turns away to tend the other end of the bar.

Dean spends the next ten minutes nursing his drink and flipping through messages on his phone. Jo sends him a last-minute text not to fuck this up. Lisa is her favorite yoga instructor at the gym where Jo also teaches self-defense and krav maga.

Dean licks his lips as he brings up Lisa’s picture on his phone. Bendy. Nice.

“Do you want another?” Cas’s voice brings him out of his quick skim of Wikipedia’s Yoga entry.

Dean shakes his head. “Better keep a clear head. My friend says she’ll kill me if this one goes badly. Just the bill, please.”

Cas shakes his head. “I’ll ask Hannah to transfer your tab over to your table when you get seated.”

Dean grins at him. “You’re the best, Cas.” He leans over to fish out his wallet and slaps a few dollars down since he’ll be paying with his card for the meal later.

Cas smoothly collects them, asking, “Do you want a glass of water while you wait?”

Dean drums his fingers against the wood. “Can’t hurt.” As Cas fills a glass he asks, “How’s the shift going today?”

“Not too badly.” Cas rests an elbow on the bar and pushes the glass towards Dean. “No difficult patrons so far, and I haven’t spilled anything on myself.”

“That does sound like a good shift,” Dean says with a grin. “I always had the last shift at the Roadhouse. Sometimes had to throw a couple of guys on their asses when they got too rowdy. Or wake up Ash when he fell asleep on the pool table.”

“The Roadhouse? The bar across the street?”

“You been?”

Cas shakes his head. “I’m always working or in class during normal dining hours. And I can’t afford to eat out very often on my budget.”

“You’re missing out, man,” Dean says. “They have the best burger. Trust me - I’ve eaten at pretty much every diner on every major highway in the US. Nobody can beat the Roadhouse.”

“I do love burgers,” Cas says wistfully.

“Then it's a fucking travesty you haven't had one yet,” Dean slaps his palm down on the bar for emphasis. “I’ll buy you one when this is all over. How’s that sound?”

Cas pauses, rag in hand to wipe down the spotless bar surface. “I’d like that very much,” he says in an undertone.

Warmth fills Dean’s chest, and he does his best to squash it. It’s not a date.

Fuck, he has one of those in five minutes.

* * *

“And then, I shit you not, he pukes not five seconds later,” Lisa says with a grin. “Big macho man couldn’t take a little heat after all.”

Dean grimaces. “The only thing I’ll be doing in 100 degree heat is wishing I’ve never been born.”

Lisa shrugs. “It’s an acquired taste, for sure. But you feel great afterwards.” She brightens. “I didn’t even get to the best part! I turn around to get some paper towels, but before I can clean it up, the asshole slips! In his own sweat! Lands face-first in his vomit pile.”

Dean winces. “Ouch. That’s gotta hurt.”

Lisa laughs. “Definitely bruised his ego.” She takes a sip of her water and casts him an appraising look over the rim of her glass. “Are you sure you wouldn't want to try?”

Dean shakes his head, a smile pulling at the corners of his mouth. “No hot yoga for me, thanks. My brother might be into it - he’s all into exercising regularly and eating rabbit food.”

“Your brother sounds like a smart man. I definitely approve of regular exercise. But nowadays most of my diet consists of chicken nuggets, mac and cheese, and fruit cups.” She bites her lip and adds quickly, “Vegetables are such a struggle in my house, you have no idea.”

Dean’s grin widens. “Sam always tries to force feed me vegetables whenever we hang out. It’s a losing battle.”

Lisa groans. "I can sympathize."

Dean opens his mouth to tell her about Sam's kale crusade of justice, but instead he catches Cas's questioning gaze over Lisa's shoulder at the bar. 

Eyes narrowed, Cas gives the least-subtle look ever at Lisa's back.

Dean low-key nods his head to tell Cas everything is alright and tries to focus his attention back on Lisa.

Throughout the meal, Cas checks in with Dean. Whenever Dean chances a glance over at the bar, there’s Cas, the self-appointed patron saint of blind dates. Dean is positive all he has to do is send one wrong look Cas's way, and Cas will swoop in like an avenging angel to save Dean's night.

He is probably mixing up his holy figures but religion has never been Dean's strong suit. He now has Cas for that.

At one point over dessert, Dean’s subtle nod is possibly _too_ subtle for Cas. He comes stalking over, only stopping when Dean meets him halfway to explain in words (he told Lisa he needed a bathroom break). Mollified, Cas retreats back behind the bar but doesn’t stop his eagle-eyed surveillance until Dean flags Hael down for the check.

“Would you want to do this again?” Lisa asks. “I had a good time.”

Dean takes more care than usual in signing his name. 

He definitely agrees with Lisa - he also had a good time, for once. But a niggling feeling in the back of his mind automatically balks at seeing her again. It's probably leftover suspicion from Amara - he doesn’t trust himself to know a good thing when it hits him over the head. He had a good first date with Amara too, after all.

“Or not,” Lisa says, ducking her head as Dean takes too long to respond.

“I-” Dean starts without any idea of how he should finish the sentence.

“No, it’s fine,” Lisa says with a smile that doesn’t reach her eyes. “If you’re not feeling it, then you’re not feeling it.”

“Can I get back to you?” Dean asks, a tad desperate. “I swear it’s not-”

Lisa laughs incredulously. “Are you going to ‘ _it’s not you, it’s me’_ me on our first date?”

Dean flushes. “Uh, not now I’m not.”

Luckily, Lisa seems amused and not angry. “I guess that’s fine. Just as long as you don’t expect me to wait around for your phone call.”

“No, ’course not,” Dean rushes to tell her, more relieved than he can say. “I might need a little time to get my shit together. That’s all I mean.”

“I don’t know.” Lisa waves off his reasons with a gesture. “It seems like you’re doing alright for yourself.”

Dean snorts. “Fake it ‘til you make it, right? There’s a reason this is a blind date and I can’t meet people in the normal way.”

“What, like over Tinder?” Lisa asks as she tips back the last of her glass of wine. “I don’t think there’s a normal way to meet people.”

Dean shrugs, his gaze drifting over her shoulder before he can stop himself. “Maybe not.”

After Dean sends Lisa away with a stilted kiss on the cheek, he ambles his usual path back to the bar, the regret already dragging his mood down like a rusted anchor. Sometimes he can’t believe himself. He had a decent date by anyone’s standards and just had to shoot himself in the foot for no fucking good reason. 

He could pull out his phone, ask her to come back so he can apologize for being a jackass in person and beg for a second date. But who knows if she’ll agree to that. He’s already shown her how much of an insecure idiot he is.

His phone stays where it is.

Cas’s voice cuts through his morose musings. “What can I get you?”

“A do-over would be nice,” Dean sighs as he thumps his elbows down on the bar.

“Was it a bad date?” Cas asks, his eyes widening in alarm. “You had said-”

“No, no, it was a good date,” Dean hurries to explain. “It just didn’t end well. My fault.”

“I’m sure that’s not the case.”

Dean shakes his head. “She wanted to see me again, and I said no like a moron.”

“Did you want to see her again?”

“Yes? Maybe? I’m not sure.”

Cas grabs a glass, nodding at Dean to continue to word-vomit his whole sad story, beginning with meeting his ex.

Cas mixes a tequila sunrise when Dean gets to Amara’s first hostile voicemail after their first break up.

“I like the colors,” Cas says when Dean raises his eyebrows in question.

Dean steadily makes his way through half of his drink as he tells Cas about Amara's unhinged, coded “messages” she’d leave for him to find. At his house, his garage, at his friends’ places. 

Dean hid out at the Roadhouse to avoid running into her, figuring she’d get bored and leave him alone eventually. Benny was all for involving the police the moment he found a letter under his door (he’s weirdly territorial like that). Dean refused. He’d never had much success with the law before.

But when Amara contacted Sam, Dean drew the line. She was clearly getting desperate, and who knows what the fuck she’d do next.

Dean slumps over the bar. “I haven’t seen Amara in ten months since that court hearing, but she still seems _with me,_ you know? My friends thought the dates would help me move on, but I don’t think they’re really doing that.”

“Maybe you’re not ready to move on,” Cas says thoughtfully. “If you’re not ready, you can’t force the issue.”

Dean sighs and glares at his glass. He’s almost down to the red part by now. “You know something about that?”

Cas jerks his head in a sharp nod. “Yes, but not with an ex-girlfriend."

Dean starts at the unexpectedly cold tone coming from his friendly neighborhood bartender. “No?” he asks, blatantly fishing for more information.

“No,” Cas confirms shortly, his forbidding expression booking no further discussion. 

Dean sighs and finishes off his cocktail. “Thanks for the drink, Cas.”

“You’re welcome, Dean.”

* * *

It’s movie night again, and Dean had a few beers before he even arrived. Thank god he did, since everyone started pestering him about his dates the moment he stepped through the goddamn door. They have all had exactly one stab at Dean’s romantic life, apparently giving them free reign to squabble over whose choice crash and burned the hardest. 

Dean spent the entire first movie (27 Dresses because Jo is a _menace)_ nursing more than a few fingers of whiskey.

Only Benny’s arrival put a stop to the badgering.

“At least you’re on my side,” Dean says without looking at Benny as a bag of popcorn shudders on its revolving tray in Charlie’s microwave. They’re alone in the kitchen, as Benny has been sending surprisingly strong glares at anyone who brings up the blind dates.

“I sure am.” Benny drops his can of beer in Charlie’s recycling and fills a clean glass with water. “After Andrea cheated, I was fucked up. I needed my friends to be there for me. Not… do this.”

“Really?” Dean asks as he leans against the counter to steady himself. “I just don’t know what’s wrong with me,” he grumbles, half to himself, half to Benny. “Lisa was fucking great. And I had to go and fuck it all up for myself.”

Benny rubs his bearded chin contemplatively. “If she’s as great as you say she is, she won’t use one mistake against you.”

Dean shakes his head, stopping only as the room spins a little too much. “At least I had Cas there.”

“Cas?” Benny asks as he shoves his water into Dean’s hand. He gently pries Dean’s fingers away from his whiskey and drains the rest of it himself before Dean can protest. 

Dean squashes down his mild annoyance (that was his drink, fuck you Benny) and mumbles, “The bartender at Angelo’s. Got a deal with him to watch my back during the dates. Did I tell you about the creep Ruby set me up with?”

“Yes, many times.”

“Cas saved my ass.”

Benny turns to Dean, surprised. “Did he?”

Dean grins. “Got me outta there in under fifteen minutes.”

“Good for him. And you.”

Dean sags against the counter and takes a hearty swallow of water. “I swear, last Friday I spent more time reassuring myself Cas was watching out for me than on my actual date. What the fuck is that about?”

“Sounds like a very uncomfortable situation, brother,” Benny says evenly.

“You bet your fucking ass it was. But it wasn’t Lisa’s fault. Or Cas’s.”

“Doesn’t sound like it’s your fault either.” He stops the popcorn a few seconds early.

Dean holds out the empty bowl to Benny. “What’re we watching next?”

“I think Jo chose Die Hard,” Benny says as he shakes the bag out.

“What the fuck? Who pairs a chick flick with Die Hard?”

Benny offers him a mocking salute with the hand not holding the popcorn. “There’s a reason I came late, chief,” he says as he turns back towards the living room.

Dean groans into his hands. At least he won’t have to drink his way through two terrible movies tonight.


	2. Chapter 2

**ANNA MILTON**

Once again, Dean is the second to arrive at his blind date - a friend Sam knows from his community garden. They have adjacent vegetable plots or some other hippie bullshit. Honestly, Dean stopped listening once Sam started on his shallots.

“Hi,” Anna says as she stands and offers her hand. “Dean?”

“Yeah, that’s me,” Dean says as he shakes it. Her grip is cool and professional, tight enough to mean business and loose enough not to be posturing. He tips his head in her direction, asking, “Anna?”

“The one and only,” she says with a little grin. “I’m so glad to meet you. Sam has said nothing but good things about his older brother.”

“All lies,” Dean says with a smile of his own. “You do know he’s a lawyer, right?”

“But I’m not,” Anna says. “And they don’t look like lies from where I’m sitting.”

Dean winks with mostly-faked confidence. “I just sat down. Give it a minute.”

Anna laughs. “If you say so.” Her mouth opens to say something else, but she pauses as Alfie approaches. She looks up. “Hi, Samandriel, I’ll have the pinot grigio."

Alfie (Samandriel?) turns to Dean. “And for you sir?”

Puzzled, Dean asks for the same. Once Alfie is out of earshot, Dean turns back to Anna. “Do you know him?”

Anna’s cheeks color. “I guess I do. This place - Angelo’s - is a family restaurant.”

Nonplussed, Dean nods for her to elaborate. Angelo’s advertises as much outside.

“It’s my family’s restaurant,” she says bluntly. “Nearly half of the staff is related to me in some way.”

“Oh.” Now it’s Dean’s turn to blush. “Uh, thanks for meeting me here anyway?”

Anna giggles. “It’s my pleasure. It’s always nice for a chance to eat here without the pressure of a quality inspection or business meeting.”

Dean leans in. “Is our waiter’s name really Samandriel? I think I’ve been calling him Alfie like an asshole.”

“Alfie is what he gives our customers,” Anna tells him conspiratorially, “and Starbucks baristas. It’s probably what he told you. Alfred’s his middle name.”

“Samandriel Alfred… Milton?”

Anna makes a face. “It’s why I let him get away with ‘Alfie.’”

Dean laughs. “Nice to know he doesn’t have a hardass for a boss.”

“I try,” Anna says, smiling brightly as Alfie returns with a bottle of wine. He glances between Anna and Dean, clearly deliberating over who should taste the wine first. He winds up pouring both of them little tasters.

Anna swirls her wine around her glass like a pro and takes a careful sip. “This is great, thanks.” She holds her glass up in a toast as Alfie retreats. “To first dates?”

“To first dates.”

She clinks her glass against Dean’s. He grins.

Dean may have fucked up his date with Lisa, but he won’t with Anna if the rest of his night goes this well.

“You own the place?” Dean asks as he looks around.

Anna shakes her head. “I co-own with my uncle Metatron and cousin Balthazar.”

Dean blinks. “Samandriel, Metatron, Balthazar? What’s up with the names around here?” He snaps his mouth shut as his face flames. Nothing like insulting your date’s family on your first meeting. “No offense,” he tacks on lamely.

Anna takes another sip of wine. “They’re all names of angels, actually.”

Dean purses his lips. “So you named the place Angelo’s? A little on the nose, if you ask me.”

“Ask Metatron,” she says as her mouth twists wryly. “He’s fond of his cliches. Balthazar and I came along later and revamped the place about ten years after he started the restaurant.”

Dean gestures to the menus, untouched on the table between them. “What do you recommend? Since you’re the expert.”

“If you’re looking for an unbiased opinion, you’re asking the wrong girl,” Anna warns playfully. 

“As long as you don’t recommend the most expensive thing, it can’t be that bad.”

Anna pulls her menu closer. “The house salad is actually really good. Don’t be put off by how plain it sounds.”

Dean tries to hold back his grimace. He actually can’t remember the last time he ordered a salad without Sam metaphorically twisting his arm behind his back.

“The ingredients are all locally sourced,” she continues, “and seasonal. Most actually come from the community garden I run? I’m sure Sam’s told you about it.”

Dean’s eyes widen in understanding. “Yeah, he has.”

“We have this program where gardeners can donate their extra vegetables,” she gushes, “since everyone sooner or later winds up with too much winter squash, every year. They trade them for credits at the farmer’s market or this restaurant.”

More impressed by her business plan than he can say, Dean takes a large drink of wine instead. “That’s awesome,” he comes up with eventually. He glances over at the bar.

Cas isn’t looking in Dean’s direction at all.

Disappointed, Dean turns back to his date.

* * *

Dean digs into his lasagna with gusto as Anna twirls her pasta primavera around her fork. “How is it?” she asks.

Dean attempts to swallow most of the food in his mouth. “Delicious.”

Anna just smirks at him and wipes her lower lip with her napkin.

Over his next forkful, Dean sneaks his hundredth look at the bar. Cas, who is muddling some mint leaves with extreme prejudice, doesn’t look up.

Either Dean lingers too long on Cas’s back, or he wears some sort of weird expression on his face. Whatever the reason, he ignores Anna for long enough she twists around in her seat to see what has caught his attention. “Are you okay?” she asks as she turns back around.

Dean drops his gaze to his food. “Yeah, I’m good.”

“Did Castiel do something?”

Dean frowns. “Castiel?” he repeats the unfamiliar name.

“Castiel, the bartender?” Anna elaborates. “He’s kind of new - he started about a month ago.”

“Oh, no,” Dean says as he mentally turns over Cas’s full name in his head. “He’s been fine.”

“Good,” Anna says with surprising relish. 

“Is he related to you too?” he asks in a casual voice. Dangerous territory, probably, but his curiosity has always been a bitch.

Anna nods, saying stiffly, “My second cousin. He desperately needed a job after he left the family.”

Dean frowns. “But I thought you were family.”

“The extended family,” Anna explains, which doesn’t help Dean at all. She sighs and idly twirls a few more strands of pasta around her fork. “They’re very... insular. A couple of us have… rebelled, so to speak. Left and joined the real world. Most come here as their first step.”

Dean swallows. “Cas said he grew up in a cult.”

Anna purses her lips. “He’s not totally wrong,” she says quietly. “I left when I was sixteen. I wanted to explore the world, experience more things than love for God. I backpacked around Europe for a bit, tried my hand at being a wandering artist. When I ran out of money, I came to Metatron.”

Dean couldn’t care less about her Euro trip. He prompts, “And Cas?”

“He left for good three years ago.”

Dean whistles. “I bet that was a difficult transition.”

“You have no idea,” Anna says, her resentment clear in her narrowed eyes and stormy expression. “Moving on, you have to do it in all at once. Like ripping off a bandaid. But Castiel had to drag it out - he tried to educate the hicks back home on his breaks from college, like they’d ever go along with his one-man Enlightenment.”

At a loss for words, Dean swigs back a large gulp of wine. He shouldn’t have heard Cas’s history from Anna. Guilt trickles ice-cold down his spine.

“It didn’t work,” Anna says flatly. “They practically cast him out; he pissed them off that badly.”

“At least you gave him a job?” Dean tries.

She makes a face. “He’s family,” she says like family deserve the barest bones of care instead of the fucking world.

Dean raises his eyes to the bar again, for the first time taking in the tension in Cas’s hunched shoulders, the slope of his bowed spine, and the angle of his head - just barely keeping Dean’s table out of his field of vision.

There’s no doubt in Dean’s mind that Cas knows exactly who Dean’s on a date with. Hell, he’s probably afraid of disrupting their evening and losing his job. Dean doesn’t blame him one fucking bit.

He musters a weak smile for Anna as he sets down his fork and knife. Time to regroup. “Gotta hit the head,” he says as he stands. On the way to the restrooms, he stops by the bar, quickly checking over his shoulder to see if Anna is watching. But she’s absorbed on her phone, a small frown on her face as she scrolls through emails or something.

“Cas?”

Mercifully, Dean doesn’t have to ask twice. Cas turns around almost immediately. “Do you need refills?”

Dean lets out a relieved exhale and smiles. “No, I think we’re good. Just wanted to stop by and let you know I don’t need your help with this one.”

Cas’s face falls terrifyingly blank. “Oh.” He looks down at the polished wood under his hands. “That’s good, then. I’m glad you’re having a good time.”

“For fuck’s sake,” Dean leans in closer, hissing, “I’m not. I’m just saying I can handle it - don’t worry. We’re not gonna have a second date.”

Cas’s head snaps up, blue eyes widening. “You’re not?”

“God no.” Dean shakes his head. 

Cas’s mouth opens and closes once before he says, “I’m sorry to hear that.”

Dean shrugs. “I’ve never had high hopes for these things anyway. But I told her I gotta go to the bathroom, so I’m gonna-” he jerks his head in the right direction. He dithers on the spot, the guilt resurfacing with a vengeance. But he chickens out and says instead, “Just wanted to let you know how it’s going.”

“Yes, of course,” Cas says quickly. “You don’t want to keep her waiting?” he asks like he’s unsure of Dean’s answer.

“The faster I go, the faster I can wrap this up,” Dean says. “See ya.”

“Goodbye, Dean.”

* * *

Anna is surprisingly hard to shake at the end of dinner. If Dean was a lesser man, he'd be all over her since she’s apparently the type who puts out on a first date. But even as Anna makes bedroom eyes over goodbyes, all Dean can see is Cas’s relieved face when Dean told him it wasn’t working out with her.

He waits for Anna’s cab outside the restaurant as he pretends to call his own ride. After her tail lights disappear around the first corner, Dean heads right back inside Angelo’s and parks himself on a stool by the bar.

“Surprise me,” he asks when Cas gets to him.

“I don’t know why you keep doing this to me,” Cas grumbles even as he reaches for a cocktail glass. “Do you like rum?”

“I’ve had my share of rum and cokes.”

“And you like sweet?”

“I guess?”

Cas rolls his eyes and reaches for a decanter of something violently yellow and a shot glass. A minute later, he pushes the finished drink in front of Dean. 

He can smell the pineapple and coconut from here. Still, he has to ask, “What’s this?”

“A piña colada.”

Dean grimaces. “Really, man?” He gamely takes a sip. Too sweet.

Cas crosses his arms across his chest. “You asked to be surprised.”

Dean snorts. “Job well done, then.”

“Not if you don’t like it.”

Dean smirks. “Guess I’ll just have to come back for another surprise then.”

Cas’s lips purse. “I suppose you’ll be back next week?”

Dean takes another sip of his piña colada. “Yeah, my friend Charlie already has her next guy for me lined up. She’s been hyping him every time we hang out with Sam - my brother. He’s the one who set me up with Anna.” Dean sighs. “They’re being weirdly competitive. Like my romantic life is their fantasy football league.”

Cas's frown deepens. “That’s callous.”

Dean exhales a weighty breath. “Or maybe I’m being a complete girl about it.” He eyes his cocktail speculatively. “It’s only one lousy night a week.”

“You’re giving your free time to these people,” Cas points out. “And, speaking as someone with very little free time himself, I relinquish it very rarely.”

Dean raises his eyes to Cas’s face. “Do you think I’m doing the right thing? Or should I tell them all to fuck off?”

Cas doesn’t answer immediately. He bites his lip, glances down the bar as if hoping for someone to call him over. When no one does, he turns back to Dean. “I have no idea,” he admits. “I don’t have friends like yours, who would care enough about me to organize something like this.” Cas fidgets in place before grabbing a rag and wiping down a spotless bit of bartop. “When I first came here, I tried to meet new people. I wasn’t very successful, and I didn’t keep at it for very long. But I admire your persistence so far, if that counts for anything.”

Touched, Dean tries to catch Cas’s eye. “It counts for a lot, man. Thanks.”

Cas glances up once, briefly. “You’re welcome.”

Dean slurps at 150% of his daily sugar intake in a glass as Cas wanders off to take care of newcomers. By now, the dinner crowd has thinned out. A couple members of the waitstaff without occupied tables mill around the hostess stand. Dean’s not super stoked to realize that they’ve all served him at one point or another in the past five weeks. Alfie gives a stoic little nod as Dean makes eye contact. Hael smiles weakly. Ambriel offers a cheerful wave.

Dean knocks back the rest of his piña colada. What a picture he must make, coming here week after week with a new person. More often than not ending up at the bar after dinner, alone. 

At least Cas doesn’t seem like the type to blab about what a sad sack Dean is.

As Dean studies Cas doing his thing, the guilt sneaks up on him again. His conversation with Anna keeps bouncing around his head. Dean tries to picture some hazy version of Cas’s parents - an old-fashioned, grey-haired couple standing on the porch of a log cabin in the middle of bumfuck nowhere. He sees Cas arguing with them in a graduation cap and gown (shut up, it’s his fantasy) before an angry mob with torches and pitchforks drive him off.

Cas returns before long, beckoned by the silent call of an empty glass. “Would you like a refill?” he asks, eyes twinkling.

Dean drags his hand down his face. He has to pull himself together. “No thanks, I think I’ve had all the pineapple my stomach can stand.”

“A water then?”

Dean nods tiredly. “Knock yourself out.”

When Cas pushes the water his way, Dean blurts, “Anna talked about you.”

Cas freezes. “Did she?” he asks, his voice deadly flat.

Heat crawls up Dean’s neck and face. He tries to belatedly explain himself, “I just thought you should know that I know... some stuff… about you.” He drifts off awkwardly.

Cas asks stares Dean down across the bar. “What do you know?” 

Dean squashes the urge to squirm in his seat like he just got caught reading someone else’s diary. “That you had a messy split with your folks.” He can’t read Cas’s face at all, so he continues, “She said you tried to help, talk some sense into them.”

Cas’s defiant expression collapses. “It was a waste of time,” he says dully. “They were never going to leave. It was foolish to try.”

“Maybe, but at least you put in the effort. That’s gotta count for something?”

Cas looks away. “Perhaps. At least, Anna was very kind to give me a job afterwards.”

“Yeah, real kind,” Dean mutters. 

Cas’s face turns pained. “She went through a lot on my behalf.”

“So?” Dean bristles, Bobby’s words from years back echoing in his head. “That’s what you do for family. They might break your heart and make you miserable, but you don’t give up on them because the going gets tough.”

Castiel stays quiet for a moment. “I suppose you’re right.”

Dean nods once, satisfied. “Sounds to me like you were fightin’ a losing battle.”

Cas won’t meet Dean’s eyes. “I thought you said you don’t give up on family.”

“But you gotta know when something’s not working,” Dean protests. “If one of ‘em came to you, let’s say five years from now, and wanted to talk. Would you tell them to take a hike?”

“No,” Cas says, affronted at the very idea.

“There you go.” Dean smacks his hand down on the bar. “Then you’re not giving up on them.”

“If you say so,” Cas says, doubtful.

Something about Cas’s vulnerable expression (or maybe it’s Dean’s own guilt for finding out something he shouldn’t have) loosens his tongue. “My brother, Sam, he had a drug problem a while ago. His college girlfriend got him into it. The day after he ODed for the first time, I tried to get him into rehab - I tried every day for the next two years. He only started listening to me when his girlfriend said she wanted to get clean too.”

Cas’s eyebrows draw together, concerned. “Is he okay now?”

“He’s been clean for five years,” Dean says, unable to keep pride out of his voice. “But the point is, he wasn’t ready for help. And nothing I said was gonna convince him. But when he _was ready,_ there was no way in hell I wouldn’t do everything I could for him.”

And yeah, Dean’s still paying off the medical debt, still has nightmares about the worst of Sam’s withdrawal, but Sam’s still _here._

He meets Cas’s gaze squarely. “That’s what it means not to give up on family. You don’t gotta knock down their door every day telling ‘em to get their heads outta their asses. Fat lot of good it did me.” He fishes around in his pocket for his wallet. “Just let them know you'll be there when they reach out - if they reach out. They might never do it, and that’s fine. That’s on them. You’re doing all you can do now.”

Dean slaps a twenty down for the twelve-dollar cocktail.

“Thanks for the therapy session, Cas,” he says without looking up.

Dean hightails it out of there before he can say another word.

**NICK MONROE**

Dean texts Charlie for an emergency breakfast Saturday morning after his blind date.

“What the fuck, Charles? _He’s exactly like Sam,”_ he hisses the moment she gets into earshot.

Charlie cringes. “I thought you might be into it?” 

“You’ve been reading too much fanfiction. Jesus fucking Christ.”

**FERGUS “CROWLEY” MACLEOD**

“I was expecting you to be taller.”

Dean’s mouth falls open. They met five minutes ago. They haven't even gotten to the dinner part, still waiting by the bar for their table to free up.

Behind them, Cas raises his eyebrows in question but doesn’t say anything.

“I’ve met your brother,” Crowley adds.

Dean gives Cas a discreet shake of the head when they’re eventually seated.

Dean angrily texts Ruby later that night demanding to know why she set him up with another asshole. 

She replies, _i hate him and i hate you. why is this so hard to understand?_

**JO HARVELLE**

Dean suspects something is up the moment Jo refuses to send him his next date’s contact information or give him a name to work with.

But it’s finally his last fucking date, so he’s going to suck it up and bear it, and probably get blind drunk at the Roadhouse afterwards. At least Benny will drive him home after his shift if Dean gets too shitfaced.

He gets to Angelo’s twenty minutes early. Hannah doesn’t even bother offering to show him to a table, just lets him slide past her on the way to the bar with a genuinely warm smile.

Cas, as usual, spots him before he can get too antsy. “Let me guess, you want to be surprised?” he asks flatly.

Dean throws him a cheeky grin. “It’s like you read my mind.”

Cas rolls his eyes and reaches for a tall glass. “I hope you know how much I don’t like this.”

“Why?”

Cas grimaces as he pours three shots of clear liquid into a mixer. “I prefer having direction. When left to my own devices, I can be a… dumbass.”

Dean snorts. “You’re doing fine, dude. Don’t overthink it.”

Cas shakes Dean’s drink, and Dean tries not to stare at Cas’s shirtsleeves pressed tight against his biceps. “I hope you like alcohol.”

“I do,” Dean drawls. “How’d you know?”

“Lucky guess,” Cas says dryly as he pushes Dean’s drink across the bar. “I had no idea what you wanted this time, so I went with a Long Island Iced Tea. Vodka, tequila, rum, triple sec, and coca cola.”

“That does have a lot of alcohol,” Dean says as he takes a sip and pulls back, impressed. He looks up at Cas. “And don’t worry about being a dumbass. We’re all dumbasses out here in the real world. Anyone who says differently is selling something.”

Cas smiles. “I’ll keep that in mind.” He gestures to the door. “When is your date arriving?”

Dean checks his watch. Hardly any time has passed. “Fifteen minutes.”

“You got here early.”

“I wanted to make sure I had time to thank you for the assist last time,” Dean says as he flashes a quick grin. “I owe you one.”

“You don’t owe me anything,” Cas says, rolling his eyes.

“Sure do,” Dean says. “You’re going above and beyond the calling of the service industry with this.”

Cas raises his eyebrows skeptically. “You used to work in the service industry yourself. Are you saying you wouldn’t do the same for any of your regulars?”

Dean freezes, his next words dying on his tongue along with his good mood.

Right, Dean is just a regular. He gets it, now. He had thought - a stupid thought because Dean’s been behind the bar just like Cas. He knows what a $2.75 minimum wage makes you do for people like Dean.

Dean can’t meet Cas’s gaze as he answers curtly, “One, I still work in the service industry. I’m a mechanic, not a Senior VP at a fancy office. B, all my regulars usually had to get kicked out of the bar at some point, so I’m something of an expert in getting people out of establishments.”

Dean takes a long pull of his drink as he mentally fights to rein in his disappointment. Can’t let that crap show and have Cas acting all concerned and shit.

It’s easy enough to figure out why Cas does what he does: it’s maybe partially monetary, but the dude has a savior complex a mile-wide. For fuck’s sake, he wants to read the Bible for a living. In terms of takeaways from a fucked up childhood, Cas could have ended up with a lot worse than a stupid calling to save everyone.

Dean’s not special. He’s just _a regular._

“I didn’t know you were a mechanic,” Cas says.

Dean shrugs as he gets up and roots around in his pocket for his wallet. “It pays the bills,” he mutters as he drop money down on the counter and goes to find Hannah about his table.

He doesn’t look back.

* * *

A whistle. “Damn, you clean up nice.”

Dean looks up at the familiar voice. “Jo?”

Jo smirks as she drops onto the empty chair in front of Dean.

Dean cranes around in his seat to look over her shoulder at the door. “Where’s my date? Are you spying on me?”

Jo gasps, drama queen loud, and raises a hand to clutch at her heart. “I’m wounded! And you’re looking at her.”

“Her who?”

“Your date, dick.”

Dean glowers as he crosses his arms across his chest. “This isn’t funny.”

“No, it’s fucking hilarious.” Jo reaches over to bop him on the nose. “Look at your face.”

“Get the fuck out of here, Jo.”

“Fine,” Jo says. “If you wanna eat alone, be my guest.”

“Did my date bail?”

“I’m your date!” Jo glares. “I swear, you must’ve been dropped on your head as a kid.”

Dean narrows his eyes. “You’re not lying.”

“No, I’m not.” she says gleefully. “Third time’s the charm, I guess.”

Dean makes a face and slowly unwinds his arms. “What exactly are you hoping to get out of this?” He gestures to the table, candle lit and everything.

“Free pasta?” Jo taps a finger against her chin. “Sparkling conversation? What else does a girl want on a fancy date?”

Dean asks in a small voice, “Uh, chemistry? Feelings?” He shudders. She’s like his sister. “A roll in the hay?”

Jo snorts. “That sailed years ago, bucko. Call this a favor to sixteen-year-old me.”

Dean sags in his seat, relieved. “So you’re really here just to fuck with me? That’s it?”

“That’s it,” Jo assures him. “And garlic bread. Can’t forget that one.”

“Gross. You’re on a date.”

“Yeah, with you, though,” Jo says with an idle wave of her hand. “I’ve seen you puke all over yourself _multiple_ times. You can handle my garlic breath. Suck it up.”

Dean smirks. “We’ll get two orders.”

Jo waves Ambriel, already making her way to their table, closer. “I like the way you think, Dean Winchester.”

Dean rarely has the chance to hang out with Jo between her waitressing and teaching. This chance to sit down with her, one-on-one, is nice. They spend most of their appetizers laughing and ribbing each other, and Dean almost forgets to check in with Cas until their main courses arrive. Once he gives Cas the a-okay, he turns back to Jo.

“Did you really not have another blind date for me?” he asks as he attacks his chicken parm.

Jo makes a see-saw motion with her hand. “Not really. To tell the truth, I was banking hard on Lisa. I thought she was perfect for you.”

Confused, Dean pauses his fork halfway to his mouth. “It’s been four weeks since that date. You couldn’t find anyone else?”

“What can I say?” Jo throws up her hands, nearly flicking part of a meatball onto the next table. “Benny got to me. You should’ve seen him at the last movie night, yelling at us for being insensitive and shit.”

“When did he do that?”

“I think you were passed out on the couch.” 

Dean flushes. “He didn’t have to do that.”

“Well, it wasn’t really _yelling._ More like a stern, guilt-tripping lecture. Like a Cajun mama bear. It was really touching. Sam almost cried.”

“Yeah, I bet.” Dean shoves more chicken in to his mouth.

 _“And,”_ Jo stabs a meatball with her fork, “he said the food here was good. That wasn’t during the lecture. He said that a couple of days ago.”

“He came here?” Dean asks surprised. “When?”

“Dunno,” Jo says through a mouthful of food. Ellen would smack her upside the head if she saw her manners. “Not while you were here though.”

“Obviously.”

“Did you know he takes shifts at the Roadhouse every time you have a date? He watches the door to this place like a stalker to make sure none of us sneak in and sabotage you or something.”

“Jesus Christ, I thought he was the normal one. You all are psychos.”

Jo salutes him with her fork. “Yet you’re the one who keeps coming back to our group hangs. What’s up with that?”

“Stockholm syndrome?”

“Beats any other theory.”

* * *

Dean lets her go with a kiss on the cheek - this is a date, after all, and Dean can be a gentleman. He only briefly debates heading over to the Roadhouse before deciding on one last drink. A strange resignation falls over him as he climbs on one of the stools, probably for the last time in a while. He waits for a minute before Cas gets to him.

“What can I get you?” Cas asks, his voice cool and distant.

Thrown by Cas's reserved tone, Dean's usual _surprise me_ dies on his tongue. “A whiskey,” he says eventually. Cas doesn't seem in the mood for teasing. 

“Is Jameson acceptable?”

Dean nods.

Cas grabs the bottle and pours Dean his drink. “You really seemed to hit it off with her,” he says stiffly as he hands it over. “I’m happy for you.”

Dean snorts a laugh as he reaches for his glass. “With Jo? Dude, she’s like my little sister. I’ve known her for her whole life.”

Cas freezes, eyes wide.

“She didn’t have anyone lined up for me, so she thought she’d get her rocks off with a friend date.” Dean takes a careful sip, licking his lips as he sets the glass back down on the cocktail napkin Cas obligingly slides his way. “So it turns out this last date was a bust. Still better than spending dinner with a creep or a perv.”

“This was your last date?” Cas asks in a soft voice.

“Two whole months of this fuckery, can you believe it?”

Cas’s head tilts as he regards him curiously. “What will you do now?”

“Enjoy my weekends again?” Dean tips back his drink. After two glasses of wine with dinner and half this whiskey, he’s almost buzzed. “I’m going to cool it on the dating. Clearly, I’m not ready for any of this crap if the only person I get along with is a girl I practically grew up with.”

“I suppose not,” Cas says in a low voice, eyes downcast. 

“I figure I should also give you a break," Dean adds. “Let you serve other people for a change.”

Cas’s head snaps up. “You won't be coming back? At all?”

Dean makes a face. Not anytime in the near future, that's for sure. Not if his common sense has anything to say about it. “I’m not the kind of guy who normally goes to these kinds of places. Dive bars, diners, they’re more my speed.”

Cas swallows. “I see.”

Cas gets called to open a new bottle of merlot before their conversation picks up again, and Dean drains his glass while unashamedly staring at Cas’s ass. Black is really a good color on him. 

Dean takes his time looking around the place. Ambriel is patiently listening to a wannabe Sally (and screw Jo for making him watch so many chick flicks) drone on and on about alterations to the menu while Harry looks dopily at her over the breadsticks. Alfie is setting up a new table. Hael is nowhere to be seen, probably in the kitchen picking up a new order. He’s feeling almost nostalgic - odd, that’s not usually what whiskey does to him.

When Cas returns, Dean already has his wallet in hand. “How much do I owe you?”

Cas shakes his head as he takes Dean’s empty glass. “It’s on the house.”

Dean doesn’t put his money away. He eyes Cas suspiciously. “You don’t do on the house.”

“One drink won’t kill me,” Cas says mildly.

Dean hesitates.

“Listen to me,” Cas says, staring at him with unerring eye-contact, “You’ve put yourself in an incredibly uncomfortable situation for whole months. You’ve been very brave. Let me give you a drink in return. Consider it one last favor.”

Mouth dry, Dean gets up. He swallows, unable to dislodge the unexpected lump in his throat. “See ya, Cas.”

Cas tips his head. “Goodbye, Dean.”

* * *

“Alright, brother, I’m cuttin’ you off,” Benny says as he takes Dean’s empty glass and replaces it with water.

Dean swears at him, loudly.

“Hey!” is all the warning he has before Jo’s palm smacks him on the back of his head. “Benny’s doing you a solid, you big drunk.”

Dean lifts his head from where it’s resting on his arms to squints blearily at her. “Shuddup, Jo.”

Jo rolls her eyes and flounces off to attend to a group of college-aged kids getting rowdy at the booth in the back.

“Come on, Dean,” Benny says as he bends down to get on Dean’s level. “Getting hammered on a Wednesday? That's not like you.”

Dean waves off Benny’s concerns and wraps a hand around his water. “I’m fine. Don’ worry about it.”

“Did something happen at the garage?”

“No.”

“Did something happen to Sam?”

“No.”

Benny exhales a weighty sigh, and Dean’s stomach roils with embarrassment, or maybe it’s all the hard liquor sitting in it. But how the fucking hell is he supposed to tell Benny he had a bad day because some religious nut ran into him on the sidewalk? Really, it was just what Dean needed during lunch break in the middle of a bad week. By the time the guy asked Dean to repent his sins, Dean was seeing red.

To make a long story short, Dean did not repent.

“Good,” Benny says, unaware of Dean’s morose reminiscing. “I can call him to pick you up.”

Dean frowns. “Why would you do that?”

“Because you can’t drive like this?” Benny asks, eyebrows raised. “And I don’t trust you not to hop the bar the moment my back’s turned and finish off that bottle yourself.”

“Come _on.”_

Benny crosses his arms across his chest and levels him a glare. “You’ve done it before.”

He has a point. 

“I’m gonna call him either way.” Benny waves his phone threateningly in Dean’s face. “And I know you. You’re going to spill your deep dark secret sooner or later. It’s your choice - me or Sam.”

Dean drops his head back onto his arms.

Benny says, “Suit yourself. At least drink some water while you wait there.”

Dean swallows wetly. Voice muffled, he asks, “Why'm I stuck in this rut?”

“You’re gonna have to say that again,” Benny drawls. “Enunciate. Go on, brother.”

Dean raises his head. “I’m stuck,” he groans. “Can’t connect with anyone. Can’t make new friends. What if this is it for me?”

Benny unwinds his arms. “What do you mean?” he asks carefully.

Dean focuses on the battered cash register at eye-level behind the bar. “None of the blind dates worked out.”

“That's not a surprise to me.”

Dean glances up at Benny, wounded. “You knew they wouldn’t like me?”

Benny rolls his eyes. “Did I say that? I said, I'm not surprised you didn’t find true love over one plate of spaghetti. You have depths, Dean. One date in a restaurant you hate isn't enough to get deep enough.”

Dean shakes his head until the Roadhouse spins too much. “So what does that mean?”

Benny shrugs. “I always thought you were the type to be friends first. Get to know someone before all that.”

“You don’t go for dudes.”

Benny jumps. “I didn’t mean _me,_ ” he says hurriedly before he catches Dean’s smirk.

Dean lets Benny’s words settle in, grimacing at the sour taste they leave in his brain. “But I can’t even make friends anymore. Where the fuck does that leave me?”

“You have plenty of friends.”

Dean snorts a disbelieving laugh. “’M not a friend. I’m just _a regular.”_

“What the hell are you talkin’ about now?” Benny asks, tossing his hands up in the air in exasperation. “And since when are you a regular anywhere that isn't here?”

“Traitor!” Jo calls from the other end of the bar.

Dean flips her off without looking. In a low voice, he says to Benny, “Across the street. The bartender - thought we were friends or somethin’. But he’s just _friendly._ Which I should’a known. I was a friendly bartender once ‘pon a time. I know how it goes.” He slumps forward, eyes closed. “So stupid.”

Benny takes a moment to respond. “You’re not stupid.” He pauses, and Dean’s stomach sinks. “Well, stupid for drinking this much.”

Dean grumbles about how very wrong Benny is under his breath so Benny won’t hear him and start a thing.

“I’ll make a deal with you,” Benny says, and the twinkle in his eyes tells Dean he heard every word. “I won’t call Sam. I’ll drive you home after my shift. But you’ll owe me a favor. Got it?”

Dean frowns up at Benny’s swaying face. Be squints, but Benny doesn't come into focus. “What’s the favor?”

“Let’s call it a surprise.”

Dean’s stomach turns over. “Don’t like surprises,” he bites out.

“Fine,” Benny says. “I’ll call Sam, then.”

“Ugh, don’t do that." The shame has already beguns its slow crawl up his neck. “He has work tomorrow. Doesn’t need to haul ass to drag me home.”

“Then do we have a deal?” Benny asks as he holds his hand out.

Dean mentally calls Benny every name in the book. “Yes, for fuck’s sake.” 

Benny hustles Dean to one of the unoccupied booths near the back, molds his slack body into a vaguely prone position, and leaves two glasses of water on the table. Two hours later, he somehow gets Dean back to his own apartment.

When Dean wakes up the next morning in his own bed, hungover as shit, he has a new text message.

 _Benny 1:27am_  
 _One more date. Your usual place @7 on Friday.  
_ _I’ll know if you don’t show up._

**CASTIEL MILTON**

Dean walks back into Angelo’s the next day with his stomach in knots and lead in his shoes. After inhaling a fortifying breath, he pushes open the door, eyes drawing automatically towards the bar.

But Cas isn’t there.

Dean pauses on the threshold, waiting for Cas to emerge from the backroom or the kitchen or something. Dean only moves when a young couple opens the door behind him to get out of the way.

Hannah looks up at their entrance, her face lighting up. “Hello,” she greets the three of them brightly. “Reservation?”

One of the kids pipes up, “Tran for two at seven.”

“Right this way,” Hannah says as she grabs their menus. “Dean, I’ll get right to you.”

Dean swallows, still looking for Cas. “Yeah, it's all good.”

He pulls out his phone to check the time. It’s a couple minutes to the hour since Dean decided not to show up early and make trouble for Cas at the bar. Turns out he didn’t need to have bothered. Instead of Cas, another man in a waiter’s uniform is taking orders and mixing drinks.

Maybe Dean will come out of this unscathed.

Hannah returns with an apologetic smile. “Sorry for the wait,” she says as she leads him into the main dining room. “Your other party is already here.”

And that doesn’t sound great. Alastair and Anna had been early too.

Dean scans the tables as they pass. Most of them are filled since it's the prime dinner hour and all. Hannah ushers him past every one, only pausing at the table closest to the kitchen doors-

Where Cas waits.

He jumps up the moment Dean sees him.

Dean only clues in that Cas had been waiting for _him_ when Cas walks around the table to pull out Dean’s chair for him.

Dean sits.

Cas hesitantly takes a seat opposite, his eyes darting all over Dean’s face. “Hello, Dean.”

Dean coughs and reaches for the water, already poured. “Hey, Cas,” is all he can manage with his dry throat. He downs about half the glass in one go. “You're my date tonight?”

“I am,” Cas says seriously. “Unless you’d rather not be here. We can call this whole thing off.”

“No, I want-” Dean blurts loudly before flushing and correcting himself, “I want to be here with you, I mean.”

Cas’s eyes widen as he blinks rapidly. “You do?”

Dean bobs a hasty nod. “I just,” he pauses, searching for the right words, “didn’t know you went for guys.”

Cas squints at him like he can’t believe what he's seeing. “I am not attracted to women at all.”

Dean nearly coughs his next sip all over the table. He recovers to splutter, “But you told me about that first date - with a woman. The one with daddy issues.”

“Which went so well.” Cas huffs a small laugh. “At first, I thought I simply wasn’t attracted to anyone I grew up with. Maybe I saw them all in a sisterly way since it’s a small community. But after I left, I still didn’t feel anything. It took a couple of tries to figure out my sexuality.”

Dean gapes at him. “But you’re… okay with being gay?”

Cas looks almost offended at the very idea. “It’s why I went into religious studies,” he says slowly. “I’m positive there’s a way to reconcile who I am with my faith.”

Dean can only stare.

“Did you think I wasn’t accepting?” Cas bites his lip. “I saw you date both men and women, and I didn’t think I said anything-”

“No, no!” Dean interrupts. “You were totally accepting. I just… assumed. So…” he drifts off, still half-waiting for the other shoe to drop. He gestures between them. “Are we really doing this?”

“Only if you want to,” Cas says earnestly. “Your friend insisted on another blind date, so I know you weren’t prepared to see me. I know I’m a bit… odd, and my people skills are not so much ‘rusty’ as completely undeveloped, so I understand if-”

“I’ve wanted to jump you since you took me to the backroom,” Dean says over Cas’s stupid rambling.

“Excuse me?”

“Goddammit,” Dean mutters as he shifts around in his seat, “I got hot for the hero act, okay?”

“Hero act?”

“Yeah,” Dean says, flushing despite himself. “You swooped in and rescued me from that creep. That hero act.”

Cas eyes widen as he stares at Dean. He swallows. “It wasn’t an act, I swear.”

Dean snorts. “You just escaped a cult. I’m pretty sure stupid pickup routines are a little beyond you.”

Cas’s mouth opens to respond, but he closes it as Alfie by their table in the same moment. 

“Hello, my name is Alfie and I’ll be your server for-”

Dean relaxes back in his chair. “I already know your name, kid. So does Cas.”

 _“Dean,”_ Cas chides. “Routine is important. Go on, Alfie.”

Alfie snorts. “What can I get you both?”

Dean glances down at the menu. Just the thought of choking down another plate of lasagna almost makes his stomach turn - even with Cas sitting across from him like all Dean's dreams come true. He pushes the menu away. “What do you say to burgers? I’m getting sick of Italian to be honest. No offense.”

Cas _glows._ “Burgers?”

Dean turns apologetically to Alfie. “Is it okay if we bail?”

Alfie shrugs. “Be my guest.”

Dean grins over at Cas as Alfie wanders off to wait on another table. “I remember promising you a burger from across the street. The best in the continental US. Whaddya say?”

Cas grabs his coat.

* * *

It was a memorable first date with Benny behind the bar and Jo waiting on them at the Roadhouse. Benny kept sending them knowing looks, and Jo nearly overfilled their water glasses three times during the meal, unashamedly eavesdropping on their conversation.

Dean found out all the boring things about Cas - what his favorite food was (PB&Js), what kinds of music he liked (all kinds), what movie he watched most recently (A Charlie Brown Thanksgiving). On the other hand, Dean got to tell Cas all about his work at the garage, about his baby, and about Sam. 

The date went surprisingly well; Dean didn't worry about how to break it to Cas that he had a restraining order on his ex or exactly why his baby brother treated his body like a temple. He didn't have to worry about deal-breaker skeletons bursting out of Cas's closet either.

With that pressure off, Dean actually chose to go through date number two entirely sober so he could drive Cas home afterwards.

Normally, Dean would have waited longer than two dates to introduce Cas to the rest of his terrible friends, but Charlie’s movie night waits for no man, woman, or handmaiden.

Dean rings Charlie’s apartment doorbell. “Relax,” he hisses at Cas as the thud of footsteps gets louder. “They’ll like you. Don’t worry.”

“Easy for you to say,” Cas mutters back as he squeezes Dean’s hand tighter - impressive, since he’d already had it in a death grip the whole ride over to movie night.

“You’ve already met Benny. And Jo.” 

“Jo made fun of my hair,” Cas complains.

“That’s ‘cause you got sex hair. It’s as funny as shit. Plus, she makes fun of my everything. It’s just how she is.”

The door is flung wide open. 

“Oh my god, you must be Cas!” Charlie exclaims before she drags Cas inside, leaving Dean standing in the doorway like the kid with a bowl cut at recess. 

“I’ll just see myself in, then!” he calls after the pair of them.

At least Sam envelops him in a bear hug the moment he steps in the living room. Ruby hovers by his side, wearing her usual sneer and says, “Nice of you to finally turn up.”

“Bite me.”

“Oh, _burn.”_

“Come on, guys,” Sam says in a long-suffering voice.

Ruby pats Sam on his upper arm. “Losing battle, babe.”

Sam frowns, but whatever he was going to say in response dies on his tongue as he spots Cas, slowly walking away from Charlie, looking a little shell-shocked.

“So this is the boyfriend,” Ruby says.

Dean flushes. They hadn’t talked about labels yet.

Cas blinks, and Dean can tell he’s mentally regrouping. “Yes,” he says serenely, and warmth blooms in Dean’s chest. “And you’re the fiancee.”

“Ruby.” She sticks out her hand.

“Castiel,” he says.

Sam glances between the pair of them, weirdly hopeful. Dean throws him a disgruntled look. Sam ignores him.

“Sam says you used to be in a cult,” Ruby says with all the tact of a rhinoceros in a ballet recital. “What’s that like?”

Cas turns to Dean, thrown by the question. Dean shrugs. He hasn’t known how to act around Ruby ever since Sam ruled out strangling her with her own hair.

Cas says carefully, “I used to be. Dean says you’re a recovering drug addict. What’s that like?”

Ruby blinks. “Difficult,” she says shortly.

To Dean’s surprise, Cas starts to smile. “I believe I can help you.” His smile widens. “Do you have time to discuss our Lord and Savior Jesus Christ?”

Ruby bursts out laughing.

Dean has never seen her lose it like this. And he was there when she heard Sam tell that stupid farting donkey story.

Sam lets out a relieved exhale, barely audible over Ruby’s guffaws.

She grabs onto Cas’s arm for support, gasping, “I grew up with a bunch of doomsday nuts. But at least they weren’t into the God talk.” She dissolves into another bout of laughter.

Dean whips his head around to stare at Sam. Sam shrugs, so she’s not lying.

Cas, completely taken aback like Dean, doesn’t have anything to say for a long moment. Eventually, he says, “I didn’t know how to use a computer until I was eighteen.”

Without missing a beat, Ruby shoots back, “I didn’t know all food _didn’t_ come from a can until I was twelve.” 

“I was taught in a one-room schoolhouse.”

“I didn’t go to school at all.” Ruby rolls her eyes at Cas’s confused look. “Homeschooled until I was put into foster care,” she adds. “My parents didn’t trust the outside world to prepare me enough for the nuclear apocalypse.”

Dean mutters in an undertone, “This explains so much.”

Sam elbows him in the ribs. “They’re bonding,” he hisses like Dean is interrupting his favorite David Attenborough documentary.

“Shut up,” Ruby says without looking at either of them.

Cas pats her awkwardly on the arm. “I bet it was hard to get up to speed with everyone else.”

“So hard,” she agrees. 

* * *

A little under a year later, Cas comes to Sam and Ruby's wedding as Dean’s date. He’s been a real trooper - listening to Dean rehearse his stupid best man speech at least a hundred times. Cas, unsurprisingly, is a good soundboard and provides decent feedback on everything but the jokes.

“You okay?” Dean asks him as they watch the newlywed couple circle the dance floor from their table. 

Cas, wearing a pensive, somewhat sad expression, turns to Dean. “Yes, I’m fine.”

“You sure you’re fine? You got that face on.”

Cas frowns. "What face?”

“The same face when your favorite discussion section flopped your pop quiz.”

Cas’s shoulders slump. "Oh.”

“Spill.”

Cas sighs and busies himself straightening his utensils. “I was just thinking about weddings.”

“Yeah...?” Dean encourages. 

Cas says in a low voice, “My parents won’t come to my wedding, if I ever choose to marry.”

Dean’s first instinct is to crack a joke, but he tamps that down. Instead, he asks carefully, “Would you even want them there if they said they’d come?”

Cas shakes his head. “I’m not sure.”

Dean reaches over to cover Cas's hand with his own. “You don’t have to be.”

“I know, but I couldn't help but think about it,” he says, gesturing around them. “This ceremony is very nice.”

Dean squeezes Cas's hand. “I’m the only family member Sam has here. I don't think he’s angsting about it.”

Cas’s mouth twists. “But you have plenty of people you regularly refer to as family. Bobby and Ellen. Benny. Jo and Charlie.”

Dean looks out at the dance floor where a number of those people are making complete asses of themselves to some Top 40s atrocity to music. “I guess.”

“I don’t have anyone like that in my life.”

Dean rolls his eyes. “Dude, you’ve been a real boy for less than five years. Give it time. You don’t create life-long bonds overnight. Charlie nearly brained me with a sword the first time we met.” Dean pauses. “And what about me, huh? Are we not like that?”

Cas makes a face but relents, “I do believe there is a more profound bond between us.”

“There you go," Dean says heartily. “With you up there and Sam by my side, that’s all the family I’ll ever need at my wedding.”

As usual, Dean’s mouth catches up with his brain a half second too late. 

Before Cas can say anything, Dean plows on, “Not that I wouldn’t murder Jo or Benny for missing the big one, but if they had to, then I wouldn’t be too torn up about it. I wouldn’t even invite Ruby if I thought Sam could let me get away with it. She’ll probably ruin it just to spite me. Even though I did _nothing_ today to set her off. I even took out that hilarious line about her lucky knife from the speech last night. It would’ve brought the fucking house down.”

When Dean pauses for breath, Cas asks, his blue eyes impossibly wide, “You see me at your wedding?”

Well, fuck. 

“Um, yeah, I guess so,” Dean stutters, his face flushing in fucking record time.

A little smile turns up the corners of Cas's mouth. “I see.”

“I bet you do,” Dean mutters. He stands, and he’s not _running away_ , he just needs to mentally regroup. “I’m thirsty,” he announces. “I’m going to get some water. You want anything?”

Cas grins up at him. “Surprise me.”

**Author's Note:**

> I'm [goldenraeofsun](https://goldenraeofsun.tumblr.com/) on Tumblr too!


End file.
